


one hundred

by orphan_account



Category: The Good Place (TV)
Genre: 5+1 Things, Awkward Dates, Background Janet (The Good Place), Dating, F/M, First Kiss, Fluff, Getting Together, Minor Injuries
Language: English
Status: Completed
Published: 2020-11-12
Updated: 2020-11-12
Packaged: 2021-03-10 03:20:50
Rating: Teen And Up Audiences
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 4,958
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/27517519
Author URL: https://archiveofourown.org/users/orphan_account/pseuds/orphan_account
Summary: Five times Michael unsuccessfully tries to take Eleanor on a date, and the one time he succeeds by accident.
Relationships: Michael (The Good Place)/Eleanor Shellstrop
Comments: 4
Kudos: 35
Collections: Fic In A Box





	one hundred

**Author's Note:**

  * For [sidewinder](https://archiveofourown.org/users/sidewinder/gifts).



If he’s being honest with himself, no, Michael does not know what he’s doing.

In fact, that isn’t accurate either.

He stopped ‘knowing what he was doing’ somewhere around the one hundred mark for reboots, and now they’re at two hundred and fifty six, and not only does he not know what he’s doing, he also doesn’t know what he’s thinking, and he most certainly doesn’t know what he’s feeling.

Because demons don’t feel... anything.

(He knows this. He has triple checked with Janet in almost every one of the last fifty or so reboots, and she has assured him that no, demons definitely do not ‘feel’. Except maybe a touch of scorn, some glee at eternal suffering, so on and so forth. Michael had stopped her there; not relevant.)

But Michael... Michael is a demon, and he’s feeling something. He doesn’t know what it is, but it’s this awful, horrible, confusing swirling pit in his stomach, and he’s pretty much got it narrowed down to three options.

The first is fear. Shaun is going to have his job and his head (that’s something humans say) if he doesn’t fix this soon. They’re hours, if not minutes, away from reboot two hundred and fifty seven, and it’s a goddamn miracle that Vicky and her crew haven’t already snitched on him (another phrase he’s learned recently, and a marvellous one at that).

The second is guilt, but he can pretty much rule that one out straight away. Sure, if he were human, he would probably be feeling all kinds of awful about screwing up the afterlives of these four specimens over and over and over again, but thankfully, he’s not. No matter how attached he finds himself growing. 

The third is something he doesn’t have a name for yet, and he doesn’t know how to ask Janet to define it for him because he doesn’t know how to explain it and he’s not sure he wants to. All he knows is that when Chidi comes to him in a crisis, he sighs, and when Tahani comes to him, he groans, and when Eleanor comes to him... he sits for hours listening to her, fascinated by the way her silly little head works.

And surely, that’s all it is? Because all humans are silly, and as a non-human, he is simply intrigued as to how they even function, when all that seems to be rattling around in those tiny heads is fresh air.

After all, Eleanor comes to him for the most ridiculous of things. Like the time she wanted a change of clown paintings; still clowns, just different ones. Or the time she campaigned for a new topping option, during the reboot with all the pizza sub places, and she went to the trouble of making posters and buttons. Or the time she asked if they could host a party without Tahani for once (he sure was tempted by that one...)

All of these things are so minor. So insignificant. If he didn’t know better, Michael might even swear she was making them up to come and see him.

But he does know better. He knows what humans are capable of, and what they’re not capable of, and he knows what demons are also not capable of. He knows an awful lot, for someone who feels like he knows so very little in this moment, and as such, the best course of action is probably to just-

A knock at his door stops him in his tracks, and he glances up to find Eleanor’s face peering in, trademark smile and bright eyes.

She goes to open her mouth, and he looks at her expectantly, and in that moment, he feels like he knows what humans mean when they say their heart soars, despite him neither being a human nor owning a heart.

So he doesn’t let her finish. Doesn’t even let her start. He panics, and he slams down the re-boot button, and he knows everyone will groan again, and he knows he has to kill Janet again but... somehow none of that matters in this very moment, because facing all of that is nothing compared to facing something he has entirely no experience with.

And since he’s already played around over two hundred and fifty times, he figures that now is as good a time as any to start conducting some smaller experiments within his experiments. If Shaun’s going to retire him anyway eventually, may as well scratch the itch.

So Michael makes a to-do list, in order of priority.   
Kill Janet  
Re-boot Janet  
Ask Janet for suggestions on human date ideas

**i. #5, The Ballet.**

Experiment number five, within re-boot two hundred and sixty, is an unmitigated disaster.

It is entirely his own fault.

Knowing his target market has been crucial in creating the perfect hellscapes for the four of them, but for whatever reason, he loses his head entirely when trying to plan something Eleanor might enjoy.

Janet informs him that many humans see dates as opportunities to try something new and/or go to an event they might not usually frequent, since it’s a ‘special occasion’. 

Michael doesn’t fully understand that logic, but he’s not going to question something he knows nothing about, so he dutifully sets up a production of Swan Lake (Vicky instantly demands the role of the Swan Queen), and swings by Eleanor’s house one afternoon with two tickets for the evening.

Her frown should have been a warning sign, but Michael’s so uncharacteristically twitchy that he doesn’t even notice.

“You look beautiful, Eleanor,” he says upon seeing her again, dressed up in an elegant blue gown with her hair falling gently around her shoulders.

“Thank you, Michael,” she smiles, seeming a little taken aback, but not displeased.

Michael files that in his head, to be added to his notes later, and nods, offering his arm for her to take.

His plan is to watch the ballet, and then go for drinks afterwards (Janet’s advice had been that dinner may be too much too soon). He can watch Eleanor watching the ballet, make a mental note of every time her expression changes, and then use those cues to initiate conversation later.

He has the whole thing planned out.

Something Michael does not foresee, however, is how much he would enjoy the ballet. Surely there was nothing to enjoy, watching demons disguised as humans twirl around a stage? And yet there he was, entranced by the story he was watching unfold, and the strangest feeling of almost choking in his throat. (These awful, awful human bodies.)

So when the lights go up at the end of Act I, he is startled. He turns to Eleanor as if he’d almost forgotten she was there, and then he grins, ready to ask her what she thought of it all, desperate to know her every thought and see if they were on the same page, see if they were both sharing in this same magic.

Eleanor is grinning back at him though, but in the strangest way, and his stomach starts to sink.

“I’ve figured it out,” she says, and Michael waits, nervously. “The dress, the date, the ballet... this... this is The Bad Place!”

“Experiment number five,” he muses later, after hitting re-boot. “This did not go according to plan. According to Janet, the end goal of a date is to establish some sort of connection. Unfortunately, Eleanor perceived our date as being such a unique form of torture that it led her to realising this is The Bad Place. I will consult with Janet and assess our options from here, though this probably rules out any future dates of a similar nature.”

Michael pauses.

“Which is a pity. I’d been looking forward to the opera.”

**ii. #44, Rollerskating.**

Experiment number forty four, within re-boot two hundred and ninety six, is a fail. (Janet informs him that all the cool kids are using ‘fail’ as a noun these days.)

Overthinking it was the root of the problem.

According to Eleanor’s file, when she was younger, she loved rollerskating. It was something her dad would take her to watch, one of the few times they actually bonded and behaved like a normal family, and even when she left home, for a few years after that, she continued to go and watch roller derbies by herself or with friends.

Her file also says that she enjoyed some obscure rollerskating films, once hosted a birthday party at the rollerskating park, and had no less than three rollerskater dolls as a child.

Her file does not mention that Eleanor never actually rollerskated once herself.

This is when Michael learns an important lesson on making assumptions, and he will not make this mistake again.

When he suggests going rollerskating, Eleanor is immediately thrilled, and this further cements the idea in Michael’s mind that this is a good date idea.

“Can I dress up?” she asks, and Michael shrugs, really not knowing or caring what the right answer is.

“Sure!” he says, matching her level of enthusiasm. 

“Awesome!” 

They go later that afternoon, to the new rollerskating park Michael has whipped up specially, and a couple of the demons are already there, whizzing around the floor and looking very genuinely like they’re having the time of their not-lives.

Michael has already set aside a pair of mint green roller skates with purple laces, the exact ones Eleanor wanted as a kid, and the gleam in her eyes when she sees them has him smiling without even realising.

“These are perfect!” she yells over the blaring music, and Michael shrugs again, because once more, he does not care, but Eleanor’s happy, and so is he.

Or at least, Eleanor is happy until they get on to the floor, and then everything changes.

“Wow, I thought I’d be better at roller skating here,” she laughs, and for the first few minutes, as they both try to find their feet and end up on the floor several times, things are lighthearted and fun.

But then they both start to get frustrated. Michael really cannot for the life of him figure out what he’s meant to be doing with these things, and Eleanor is nervously edging her way around the floor, clutching on to the sides for dear life.

As if things couldn’t get any worse, while Michael is on the floor, trying and failing to get back on his feet, Bambadjan then appears, holding out a hand to Eleanor, who gratefully accepts it.

The next moment, the two of them are flying around together, Eleanor laughing, her hair flying out behind her, and Michael is livid that Bambadjan has stolen his date from him.

He has nothing to fear on that front though, because not long after that, Bambadjan misjudges Eleanor’s confidence, and lets go of her, clearly expecting her to sail on by herself, star of the show.

This is not what happens, at all.

“Experiment number forty four,” he begins, voice heavy. “We’re having to re-boot, since Eleanor decided that if she can break both of her legs and an arm, this can’t be The Good Place, and therefore it has to be The Bad Place. Note to self: do not assume that childhood interests equate to any sort of skillset. Also note to self: rollerskating is a terrible human activity, and further proof of why we should be torturing all of them.” 

**iii. #67, Stargazing.**

Experiment number sixty seven, within re-boot three hundred and fourteen, does not go as planned.

This one should have been marginally more frustrating than the others because he had to make additions to the neighbourhood itself to pull it off, and it still didn’t work, and yet... 

Eleanor is, at least, receptive to the idea of this one. 

“Michael... what are you doing here so late?” she asks, when he shows up on her doorstep one night.

“I was out walking, couldn’t sleep. Wondered if maybe I wasn’t the only one,” he says, tilting his head toward the lights still on in her living room. (He wasn’t out walking; he has asked Janet to monitor Eleanor’s house every evening and inform him when she stays up later than usual, and she finally delivers on day ten.)

Eleanor laughs, a little sheepishly, and something inside of him twists in a strange yet somewhat delightful way. She peers back up at him and shrugs.

“Yknow, yeah, actually, same. I couldn’t sleep. Sounds ridiculous, right? Surely you don’t get insomnia in the afterlife?”

(Michael has the decency to feel a little ashamed that he files ‘insomnia’ away in his ‘return to this later’ folder.)

“No, I get it,” Michael laughs with her, as if he really does get it. “Say, do you want to join me on my walk? Everything’s better with company.”

He can see her debate it for a short while, and there’s something akin to hope bubbling up inside of him, which turns to relief when she nods.

“Sure, why not?”

Michael waits for her to grab a jacket, and then they set off together, meandering around the paths of the neighbourhood until they reach the large patch of grass near the lake. 

Somehow, they don’t run out of things to talk about while they walk. Janet has told him horror stories of the awkward atmospheres that ensue on ill-matched dates, and Michael’s terrified that everything will feel different between the two of them now that he’s got a new agenda, and it does, but somehow that isn’t a bad thing.

Eleanor just talks to him, the way she always does, her unique mix of comedic storytelling about neighbourhood events, interspersed with anecdotes from her previous life, and every so often, a general observation on their surroundings, or a question posed to Michael. And he answers every one of them, most of them honestly, and finds himself asking questions in return, eager to learn more about her.

For the first time, Michael does not feel like he is gathering intelligence, but just knowledge. Further knowledge of all of the parts that make up Eleanor Shellstrop, and he is enamoured with every one.

“Hey, the sky is pretty clear tonight,” he drops in casually, when the conversation reaches a natural lull.

“Huh, I didn’t notice,” Eleanor says, glancing up.

“Do you want to stargaze with me?”

He’s expecting a snort and a rejection, but everything feels different in the early hours of the morning (despite time being a complete construct here), and he hears Eleanor agreeing, plopping down into the grass and leaning back so she can look up at the sky properly.

“Do you know any of the constellations?” she asks, tilting her head. “I mean, are they even the same constellations here? Is this even real?”

“Does it matter?” Michael murmurs, not watching the sky, but instead watching her, and the way his carefully designed stars sparkle in her eyes.

“Guess not,” she laughs, and falls silent again.

Michael does look up at the sky after that, and though he doesn’t fully understand it, he sort of understands why humans like looking at this thing. He supposes that for their simple minds, something glittery and seemingly never-ending is an interesting concept.

“Eleanor,” he begins, after they spend a comfortable five minutes in silence. “I-“

He is stopped in his tracks by the sound of soft snoring, and when he looks over again, Eleanor is soundly asleep, the light of the moon casting long shadows beneath her eyelashes.

Somehow, Michael isn’t even bothered. Sure, he doesn’t think dates are meant to fall asleep on one another, but she looks so peaceful now, and knowing he has actually helped her get a good night’s sleep... well, he doesn’t know how to explain it, but there’s a warmth inside of him that wasn’t there before, and he likes it.

“Experiment number sixty seven. Although nothing happened tonight, I still had a nice time. And I believe Eleanor did too. And although nothing has come of it... I think it has been enough for me.”

**iv. #93, Salsa Dancing.**

Experiment number ninety three, within re-boot three hundred and seventy five, almost works, until it doesn’t.

Janet is fast running out of date ideas, which means Michael is fast running out of date ideas.

They have pretty much got the formula nailed by now; it needs to be something interesting enough for Eleanor not to assume she’s in The Bad Place, romantic enough for her to understand it’s meant to be something resembling a date, safe enough that she doesn’t get hurt (the skydiving incident... Michael still shudders thinking about it), and normal enough that she doesn’t freak out.

There is a very narrow window in there in which Michael is trying to find success, but he’s struggling.

So when Janet starts suggesting some more ‘out-there’ ideas, he figures, why not? At best, things are going to work out, and at worst, he just has to hit the re-boot button. Again. At least the saving grace is that with his new project, the rest of the demons are getting to try out new roles, which he thinks they’re all appreciating. Anything to keep them on side.

They cycle through paintballing (too dangerous), laser tag (done that) and an engineering workshop (“Janet, please.”) before salsa lessons appear on Janet’s radar.

“Now that could work,” Michael considers, and nods. “Yes, we’ll do salsa lessons. I can wear a fancy bow-tie and everything.”

To sell it, the salsa lesson is a whole neighbourhood affair, with anyone who wants to join in invited to Tahani’s house - her second ballroom has ample space for them all to fit. Eleanor drags Chidi along, much to Michael’s dismay, but then to his delight, Chidi stays firmly seated on a chaise longue at the edge of the room, leaving Eleanor partner-less.

“May I have this dance?” Michael asks from behind her, internally congratulating himself on how smooth he sounds.

“Michael,” Eleanor exclaims, surprised, but seemingly not unhappy. “I would love to.”

With a smile, he leads her out into the middle of the floor, where there are around ten other couples waiting for instructions. Tahani and Jason (he must do something kind for Jason soon; yes, this is hell, but Tahani is Tahani) are stood facing them all, ready to be the demonstration pair.

“I should warn you, I have two left feet,” Eleanor whispers to him, and Michael smiles down at her, endlessly endeared by the way she makes light of any situation possible in order to make everyone feel more at ease.

“Well, I have two right feet, so I think we’ll be okay,” Michael whispers back, with a conspiratorial grin, and Eleanor laughs, properly, and loud enough that everyone turns to them.

They both look around, nodding apologetically for the interruption, but Michael isn’t sorry at all. He feels like he’s flying.

Salsa dancing, as it turns out, is something that necessitates standing very close together, with hands on hips and waists and legs pressed against one another and hot and heavy breaths landing on each other’s necks.

Until now, their dates have always been very sweet affairs, but this is the first time Michael feels things shift into something different, something new, something a little deeper and maybe even darker. 

As Eleanor leans into him, a spin forcing her into a position where her back is against his front, her head in the crook of his neck, Michael almost loses his head, before she’s spinning back out again, and they resume the footwork they’ve been learning, two, three, one, two, three.

The music crescendoes as they move into the last few steps of the routine, and the rest of the neighbourhood seems to melt away around them (Michael is fearful that it does, in fact, literally melt away for a moment, and has to blink to realise everything is still standing, it’s just not important right now). 

They move into a dip, Michael’s arms moulding to the lines of Eleanor’s petite body, and he leans in. Eleanor looks up at him, eyes dark, glinting, and then she moves closer to him, lifting her head slightly, and where Michael would have a heart, something is thumping-

“And finish! Great work everyone.”

Tahani’s voice breaks the spell, and Eleanor nearly topples over in her shock.

Catching her, Michael brings her up to balance again on her feet, and she smiles at him shyly before hurrying over to Chidi.

“Experiment number ninety three. No more group activities,” Michael vows later on that night, recording his notes as usual. “No more group activities.”

**v. #101, Funfair.**

Experiment number one hundred and one, within re-boot three and ninety seven, is Michael’s hail Mary.

After over a hundred dates, he’s starting to give up on this whole idea. After all, what is he even thinking? He’s a demon, and he’s meant to be torturing these humans, not choosing one of them as a side project on which to test out his newly discovered range of human emotions.

He doesn’t view Eleanor as a side project though, and that’s a lot of the problem.

She is the main event for him now. Although she’s been re-booted hundreds of times, never remembering any of their ‘dates’, Michael’s memories of the time they spend together go nowhere, and nowadays he spends most of his time just daydreaming about all of the hours they’ve spent together.

Janet tells him that the closest word for what he’s feeling is ‘lovesick’, which makes him feel very silly and very giddy at the same time.

That giddiness is what drives his idea for this date, which he vows will be his final attempt. If they can’t figure it out this time round, it’s clearly not meant to be.

Except, it feels like it’s meant to be.

When they’re laughing together on the dodgems, Michael driving and Eleanor throwing her head back with laughter. When they’re waiting for cotton candy, and Eleanor steals a bit of Michael’s because she’s too impatient, and ends up with a face covered in sugar for her troubles. When they’re at the top of the ferris wheel, and they can see the rest of the neighbourhood, and the stars above them, and everyone else below them, also laughing and having fun, and everything feels perfect in this moment.

“I never thought I’d get to The Good Place,” Eleanor says softly, as she takes in the scene alongside Michael.

(His stomach lurches, uncomfortably, but he tries to force the feeling back down, determined to be in the moment. Romancing Eleanor is his focus at the moment, not torture.)

“Do you like it?” Michael asks sincerely, twisting to face her properly.“I do,” she breathes out, nodding and smiling. “I really do. It’s perfect.”

She looks around for a while longer, before her gaze settles on Michael, who is looking right back at her.

“I’m glad,” he says eventually, and she smiles.

“Thank you, for all of this,” she says, gesturing to it, and he shakes his head.

“My pleasure.”

A beat of silence passes between them, and then Eleanor shifts in her seat as they begin to descend back down. Michael tenses, preparing himself, and then Eleanor is leaning closer to him, closing her eyes, and he’s closing his too, and then-

And then she drops a gentle kiss on his cheek.

“Perfect.”

Michael’s fingers linger on that spot long after the funfair has ended and Eleanor has gone home, and they continue to rest there as he records his thoughts.

“One oh one,” he says softly. “And with that, we conclude the findings of this experiment.”

**+i. #102, Drinks.**

Re-boot four hundred and thirty seven. Jason is Jianyu, Tahani is living in a tent on a mountain, Chidi can only borrow books from the library for twenty four hours, and Eleanor’s entire house is shaped like a clown’s head. There are many, many bars in the centre of town, all serving carbonated drinks with a one per cent alcohol content, so that you become too bloated before you can get drunk.

Michael is sat in one of said bars, nursing a glass of sparkling elderflower, pouring his heart out to Janet, who is nodding kindly and offering nothing in the way of reassurances.

“I just thought it could work,” Michael says sadly, tracing the rim of the glass with his finger. “I thought I made her laugh, I thought I made her happy. I thought I saw something in her eyes a few times that seemed to match what I was thinking.  
“And sure, I knew it probably couldn’t last. I’m an architect, and a demon, and she’s a human, and my job here isn’t to find love, or happiness. In fact, it’s to make sure those four never feel happiness again. And yet, I thought if we really, truly were meant to be together, we’d find a way to make it work. I guess-“

“I will have a large glass of your best lime, and a top-up for whatever the distinguished gentleman next to me is drinking.”

Spirits lifting just at the sound of her voice, Michael turns in his seat to find Eleanor sat next to him, beaming.

“Eleanor,” he says by way of greeting, feeling some of his woes melt away just from the force of that smile.

“Michael,” she returns, sliding his fresh drink over to him. “You look like you need a friend. And a drink.”

“Oh, I’m fine,” he protests, grabbing the new drink and holding it up to her. “But thank you.”

“Okay, then I need a friend and a drink,” she counters, getting comfy on her barstool, and Michael shrugs. He can’t argue with that.

“To friends and drinks,” he suggests, and she smiles, clinking her own glass against his.

“To friends and drinks.”

They sit in that bar for hours.

Long after they’ve tired of their drinks, the half-empty glasses forgotten on the bar next to them, they chatter away.

Michael finds that, strangely, without the pressure of wanting to impress, it is easier to talk to Eleanor than ever. Their conversation reminds him of the night they went stargazing, Eleanor’s topics just as varied, unfiltered and honest now as they were then. 

And Michael returns this, tenfold.

As far as he can, he tells her about life as a demon, working his way up to becoming architect, everyone he’s dealt with along the way. He tells her his hopes and dreams for the future, and she shares with him her past and her present, and all the while she’s gesturing wildly, face alight with expressions and reactions to his stories. She laughs and she sighs in all the right places, and her eyes sparkle when she’s talking about something she loves, and Michael has never felt more hopelessly in love with Eleanor Shellstrop than he does that night.

“Bar’s closing,” they are informed, and they both look around, surprised to find that it is dark outside, and they’re the only ones left.

“Walk with me?” Eleanor asks, instantly, and Michael nods, not wanting to leave her side for a second.

Their conversation continues outside, the balmy evening air of a perfectly designed neighbourhood creating the perfect ambience as they walk.

They take the long way back to Eleanor’s house, round past the lake, and all the while, they continue to talk, to share thoughts and ideas and feelings.

“You are incredible,” Eleanor says suddenly, interrupting a story Michael is telling about a neighbourhood he’d built during his earlier years as an apprentice.

They are next to the lake, the water rippling, and the leaves in the trees above them rustling. It’s as perfect a setting as any Michael had ever conjured up, but this has nothing to do with him.

He blinks at her, surprised at the comment, but thrilled to hear it.

“Incredible?” he repeats, and she nods.

“I had no idea you were this interesting,” she laughs, and his face falls for a second, feeling as though they’re about to drop right back into ‘kiss on the cheek’ territory, but then she steps closer, peering up at him. “Interesting, and funny, and knowledgeable. You’re incredible.”

Michael is at a loss for words, which, fortunately for him, Eleanor seems to find sweet.

“I don’t know how the afterlife is supposed to work,” Eleanor says softly, reaching up to brush her fingers against the very spot on his cheek she’d kissed not too long ago, “but I’ve always liked the idea of finding a soulmate, eventually.”

“Me too,” Michael murmurs, and he didn’t realise it until this exact moment, but he agrees.

“Well I don’t know what the rules are on architect-resident fraternisation, but-“

“To hell with the rules,” Michael says, and for the second time only in his life, acts on instinct, spontaneity, and happiness.

He kisses her softly, gently, with the respect she deserves, but also with the feeling of a hundred moments shared before this one, and a thousand days spent in each other’s company. He kisses her with the knowledge that they could both live forever now, if they so chose to do so, and he could do this every day for the rest of time if she wanted to as well. He kisses her with a force he hopes conveys how much he loves her, every version of her that he’s ever met.

She kisses back in a way that suggests she loves this version of him, the only one she ever remembers meeting, but who is enough.

“One oh two,” he says later, back in his office, head spinning. “I feel... that this has been a success.”

**Author's Note:**

> I've never written this pairing before, and I didn't even sign up to write TGP, but I'd just finished re-watching when the prompts for these came out, and I decided to take a stab at it. I really hope it worked, and that you enjoyed!


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